


A Date with Mary Vanderwood 3rd!

by LittleToxic



Category: Mystic Messenger (Video Game)
Genre: Cowgirl, Crossdressing, Date Nights, Deep route, Explicit sexual scenes, F/M, Fluff and Smut, Gambling, Husband and Wife??, MC Choi, Mary Vanderwood 3rd - Freeform, Messenger, Mystic Messenger - Freeform, Other, Otome - Freeform, Punishment, Saeyoung Choi - Freeform, True Love, crossdressing sex, cute dresses, lovemaking, zen - Freeform
Language: English
Status: Completed
Published: 2016-12-28
Updated: 2016-12-28
Packaged: 2018-09-12 23:27:54
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 3,246
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9095380
Author URL: https://archiveofourown.org/users/LittleToxic/pseuds/LittleToxic
Summary: You have finally beaten Saeyoung in his own little betting game. Now it was payback time! What kind of punishment should you inflict on your favorite hacking genius? You have always loved how he looks in a dress....





	1. Chapter 1

“Ha!”

 You jump up from the wooden floor and drop the console. Saeyoung is too stunned to scold you for dropping his controller because he can’t believe it. He looks at the screen, and back at you, who is in mid victory dance, shuffling in your owl-printed socks on the wooden floor. You’ve won. You’ve actually won!

“I sooo kicked your ass, Saeyoung!”  You cheer with your hands up in the air and then you freeze, getting a mischievous look in your face that makes Saeyoung’s lips lift up into a nervous smile.

“What’s with that creepy look, YN? You are scaring the crap out of me.”

You stay silent as Saeyoung stands up. He wears a thin gray pajama bottom with a tux wearing cat printed all over it. Those adorable mustached cats remind you of all the bets you’ve lost, but the most memorable one was when you were posing as a cat for him. You were forced to say “meow” after each sentence and ignored if you didn’t do it. You had a collar and everything.

OHHHHHH, he would pay!!!

****

**_Saeyoung, could you please give me a roll of toilet paper? –Silence- Saeyoung!_ **

**_~Lalala~ I can’t hear a word, unless the magic word is spoken._ **

**_Saeyoung, meow, could you give me some toilet paper, you asshole, meow!_ **

**_Good girl._ **

 

You give an evil laugh. Those evil laughs where all it needs is the thunder and lightning. He sees the crazed look in your face as you continue to laugh on your own. He was in trouble now.

Saeyoung was now hiding behind the (color) couch peering at you from the arm rest. What exactly was going to be his punishment for losing? You definitely looked like you had lost it and he was, frankly, starting to feel uneasy.

You walk over to him super slowly, pulling down his (color, design) t-shirt over your undies. “Oh, Saeyoung, you’re not hiding from me are you?”

The malevolent singsong in your voice makes him gulp. He stands up from where he is, “Ah..Um..I would never. Have I told you how beaut--?”

“Shut it!” You cut him off, your finger pressing the tip of his nose “I have decided what your punishment will be.” You cross your hands over your chest and close your eyes “We are going on a date.”

His sigh of relief is loud and immediate, but before he can even think of anything to say, he catches a flash of that naughty gleam in your (color) eyes.

 “Buuttttt---as you dressed as Mary Vanderwood 3rd”

You attempt another evil laugh, but Saeyoung simply says, “Sure.”

You smirk at him, “Just make sure you don’t lose character before I say it’s over or no _sex_ for a week.” You raise a finger at him, “One mistake and it’s over.”

That definitely struck him, you cheer victoriously inside.

 “Aw c’mon, why do you have to be so heartless?” He blinks big golden puppy-dog eyes at you.

“Karma, that’s why!” You give him a wicked smile, “Goodbye Saeyoung. I only speak to Mary from now on.”

He ruffles his red hair, “Agh!”

You take off his t-shirt, revealing your naked breasts and your mound that is covered by those (color) panties. He bites down his lip at the sight.

“And, remember, just one mistake and you won’t suck on these for a week. “He almost shoots blood through his nose when you cup them in your hands. He sinks on his knees as you saunter to the room. He had created a monster, a beautiful monster with perky tits and the face of an angel.


	2. Chapter 2

 

          The day has come. The day of Sae—no, Mary’s, date with you. Saeyoung slips into the ribbed (color) sweater dress covering his (color) women’s panties that can barely hold his cock in. You had picked out the most girlish underwear you could find with ribbons and frills. The dress zips from the front, from where the cleavage is supposed to start, to the hem that falls just slightly above his knees. The merlot wig is already on his head and sleek strands of straight hair fall over him as he leans over to put on the (color) wedged boots over sheer stockings. He stares at himself on the tall floor mirror that decorates the corner of the room you both share.

The moment that you exit the bathroom and you take him in, you are in awe. He is gorgeous. That dress hugged his tall frame in all the right places. His reflection meets eyes with your (color) ones.

“How do I look?” He asks.

You go towards him and you hug him from behind, “Oh, Mary. That dress looks lovely on you.”

You gaze at him through the mirror. The long of his neck looked so sensual, so very tasty. Since he didn’t have a pronounced Adam’s apple, it allowed him to convincingly pass as a woman. Your hands roam slowly down his narrow hips and he captures your hand quickly and you smile to yourself to see how beautiful that (color) manicure looks on him. He brings your hand to his lips.

“Oh, miss. I still need to finish getting ready. If you play with me now, we will never get out of here.”

You smirk at that cutesy tone in his voice, he was good at this, too good. You slap his ass as you turn to finish getting ready yourself. You wear cat stockings that reach below your knee and a (color) suede skirt. You don’t see the hungry look in his eyes as you disappear into the bathroom.

**~Date with Mary Vanderwood 3 rd~**

You walk through the streets of downtown, your arms locked on Saeyoung’s elbow as the sun begins to set. If you hear another whistle directed at Mary, you swear you are going to pull your pigtails right out of your scalp.

“You seem angry.” Saeyoung leans his merlot head against you with a little smirk lifting his pink painted lips.

“You don’t even have boobs and you are still getting catcalled.” He stifles a girlish giggle with the back of his hand.

 “You need more than just breasts to attract a man, YN. You should know that.”

You roll your eyes as you both continue strolling past shoppers, couples, their voices humming around you and being left behind as you both get lost in your own world. You come across a claw-machine right outside a convenience store that is lighted in all variety of colors, you both hurry towards it.

Saeyoung digs through his fringe purse as you push your forehead against the machine. You already know what you want! You fall instantly in love with an adorable alien girl plush with a purple bob. You look over to Saeyoung who is still digging through his purse when two guys interrupt, who have just exited the store.

“You girls want us to win something for you?”

Saeyoung makes an irritated sound as you nod, turning to grab Saeyoung by the elbow.

“What are you doing?!” He whispers harshly into your ear.

“Free toys are always good, no?”

He shakes his head no at you as you lead him towards the two men, who are already digging through their jeans for change.


	3. Chapter 3

                “Damn it! That alien girl is really stuck in there. I could only get you the duck.” Joon, one of the guys, says as he lowers to grab the stuffed toy and hands it to you. You take it with a smile as you glance over at Mary who is not in a good mood anymore.

 An aura of irritation steams from Saeyoung, which he hides under a fake smile as Kwan says something close to his ear. Saeyoung tilts his face away from his braided beard as he grips the stuffed bear he received in a death grip. 

“You’re quite tall, baby.” Kwan tells him in a voice that deepened in an attempt to be smooth. He is going to kill you! This guy’ breath smells of rancid beer and hot wings.

“Am I? I hadn’t noticed.” He says quietly staring over at you as Joon, who didn’t look as shady and gross as this one, handed you another stuffed toy. He tried to hide the nagging jealousy boiling inside him.

“Why are you getting sarcastic? Don’t you like me, baby?”

He slithers his arm over his waist and pulls him to him. You give a quick glance and notice immediately the crazed look that has overtaken Kwan.

“Hey! What the hell are you doing?! Leave her alone!”

You attempt to run towards him, but Joon jerks you from the wrist making you drop the two stuffed animals in your hand, “Calm down, sugar. Kwan doesn’t mean no harm. Why don’t you give me a kiss to repay those little plushies I got you, huh?” He lowers to try to give you a kiss, but you slap him as hard you can with your free hand and he shakes you, “You little bitch!”

“Let me go!” You fight

Saeyoung punches Kwan, knocking him cold as he runs towards you. Everything happens so fast that before you know it, Saeyoung is grabbing you by the wrist and you are both running. You are panting now and you only relax when you are inside the Lamborghini.

You catch your breath as he turns on the car. Although the engine is humming, Saeyoung doesn’t drive. You stare down at your hands, suddenly overrun with guilt. You ruined your date, and put both of you in the path of two assholes. What would’ve happened if they had discovered that Mary was a guy? You are choked by a flash of fear.  You place a shaky hand on Saeyoung’s exposed thigh.

“I am so sorry, Mary. I-I shouldn’t have done that. That could’ve gotten so bad.”

You look towards him as the moon glows through the window and shines over his strong chin and sculpted lips. You miss his glasses.  He doesn’t say anything for a few seconds, when he suddenly erupts in such a loud laugh that it makes you jump on the leather seat. 

You frown, “What’s so funny?!”

“I can’t believe that you are still calling me Mary, even when we were going to get assaulted by those sleaze bags!”  

“You are breaking character!!!!”

He reaches over your seat to give you a soft kiss, “Are you alright, miss?”  You nod, returning his kiss, suckling on his lips until that pink lipstick is completely off him. 

“I want to make love to you, Mary.” You whisper between kisses, putting your hand between his legs.

 


	4. Chapter 4

By the time you enter the penthouse the events of earlier were long forgotten. Toeing off boots, throwing purses on the ground, you enfold your arms tightly around his neck and he grips yours hips pressing you against him, his bulge starting to harden under his dress. He guides you to the bedroom never leaving your neck, making you shudder. He stumbles slightly over thrown dirty clothes, but he never loses his balance or lets you go as he licks over your jaw. Once inside, you pull away with a kiss and spin him around to push him back on the bed.

He looks at you with an intense hunger and you are aroused and proud of the fact that Saeyoung’s eyes have only looked at _you_ like this. His burning gaze feels like caresses over your hot skin as he breathes heavily at the way you begin to unzip his dress, giving open-mouth kiss to every piece of skin that becomes exposed. Brushing wine colored strands over his shoulder, you lean over his spread legs to take a nipple into your mouth, he grips your hips with a sharp intake of breath as you begin torturing the harden bud with the tip of your tongue. You trace your way to his other nipple and lick up your way to his neck, you feel his cock hard against your belly while you suckle the skin there. When your lips find his earlobe he lets out a shallow groan, he slides his hands down your clothed back and as if just noticing that you were still clothed, he begins to fumble with the buttons on your skirt. He yanks it down with a force that makes your breasts jump. It pools at your feet as you continue caressing his body with your tongue, licking his clavicle, tracing them with the tip of your tongue.

“You taste so good, Mary.” You say croakily as he looks at you with narrowed eyes blurred with desire. He yanks the buttons on your blouse, to horny to even take the time to unbutton them. To his relief you aren’t wearing a bra and he leans in, pushing you back to place his face between your breasts. You squeeze them together pillowing them for him as he suckles hungrily.

“Mmm…” You mumble in pleasure.

You pull the long strands of hair away from his face and when you try to pull away he grips your ass, his fingers entering your panties from behind, tracing the cleft of your ass down to your soaking pussy. You hear his growl when he feels your wetness coat his fingers. It feels so good to feel his strong fingers rubbing back and forth your slit, savoring your slippery flesh and when he probes your entrance you freeze.

 “Be a good girl, Mary.” You whimper as you pull away hesitantly. He looks at you with a look that tells you that he can’t be teased any longer, but he nods and brings two fingers to his mouth to lick the honey you have left on them. You shudder at the sight as you undress completely and fall on your knees, sinking into the beige carpet. You pull his dress up to find his hard cock pushing against the thin (color) panties. It looks so tasty there. You lick your lips at how the naked head peeks from the frilly rim. It is so wet already. You look up at him, massaging his cock over the panties, tracing the outline of it with a gentle squeeze that makes him groan.

“Mmm...” you moan impishly, “look how hard, and wet you are Mary.” Your thumb circles that white cream on the slit of his penis as he fists his hands at the sensation. You lower to give the head a tiny lick and stop to look up at him.

“Don’t tease me.” He strains between clenched teeth. You hear that little warning on his voice, that pleading.

You press your cheek against his cock, feeling the girth of it against your face. You can feel the way it pulses with need against the fabric and you look up at Saeyoung as you cup his sac.  His jaw clenches as he brushes the hair from your face so he can enjoy the way you rub your face against him. There will never be anyone like you...

“It feels so good.”

“You are so naughty, YN…” He breathes and agreeing with him, you lick up the length of his cock over his panties and cover the mushroom shaped head with your warm mouth and begin suckling it. He fists a pigtail in his hand as you slurp nosily, pulling down the panties with one finger. You take in as much of that velvety hardness as your mouth can allow. His hips move against you and he pushes your head down demanding more. At the feel of his plea you suction him tighter, cupping his balls at the rhythm of your bobbing. He groans at the intense pleasure of you torturing him with your mouth, with your hands. He tightens his eyes. He doesn’t want to cum like this. He wants to cum inside you. He grabs you abruptly from the arms pulling you up from between his legs.

“I want to be inside you. I can’t take anymore---M-miss.”

You know how hard he is working to stay in character so you oblige, climbing up on his lap. You rise enough to pull your panties aside as he impales you impatiently. You throw your head back at the sudden thick invasion, but your wet core welcomes him eagerly. He slaps your ass with both hands and cups you, moving you to his hungry rhythm, thrusting under you. It is so erotic the way he drives into you, wearing that dress in a strange way, made him manlier to you. The dress rubs against your tummy as you ride him, and you start feeling your orgasm building deep within you, tingling your toes, making them curl as you move along with him, trying to keep up with his pace that has become relentless. You don’t feel like you can take anymore and you lose yourself in that earth shattering bliss. Each pump taking you closer to release. A release that only the man you love can give you.

The man you can’t live without.

“Saeyoung…” Your murmur into his neck. Hearing his name on your lips is enough to make him cum.

“My- name-is-Mary-remember?” He thrust fast and deep in emphasis with each word that it makes you scream out.

You look up at him, his frantic pumping never ceasing.  He loves the moans that escape your lips without your control, the lopsided pigtails that jump with every movement. The way your nipples rub against him. You yank that wig off along with the cap, until his tousled red hair is revealed once more, “Screw, Mary. I want my husband back.”

You cover his lips that are smeared with lipstick before he says something witty. “OH, Mr. Choi. I’ve missed you.”

“I missed _you,_ Mrs.Choi.”

Locked together, your bodies moving in the frenzied rhythm of your lovemaking, you orgasm simultaneously until all you can see are stars and all you can do is scream out his name and he _yours_.

 


	5. Chapter 5

Saeyoung looks down at his playing cards as you jump up in the air and spin on your bare feet.

“I won!” You laugh heartily and drop with your legs under you to give him a smug smile. You pull the spaghetti strap from your thin (color) camisole over your shoulder as you begin rocking from side to side in excitement.

“You must be cheating me in some way.” He utters stunned, putting down his cards and raking his fingers through his red tresses. He never, ever, lost at poker.

You stick your tongue out at him in response as you scan your husband slowly, who wears nothing but gray boxer shorts, which are printed with green little alien heads. Beside him, on the couch, sits that adorable alien girl plush with her purple bob and he rapidly grabs it preparing himself for the blow. He winces at the naughty look that begins to form on your face as he waits patiently while you scan him, thinking of all the new ways you plan on torturing him. He should’ve ended this game a long time ago. He jumps when he hears your voice. You tap your chin with a wicked smile curving your lips,

 “From now on, you will call me mistress, Saeyoung Choi.”

God you were crazy. God he loved you.

“Your wish is my command, mistress.” He says, crawling over to you like a very good boy.

**Notes for the Chapter:**

> Hope you liked! Thanks so much for the views and kudos. ~_~


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